[ CAS No. 2094-72-6 ] {[proInfo.proName]}

Name: 2094-72-6|1-Adamantanecarbonyl chloride|98%
Brand: Ambeed
SKU: A377388
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Quality Control of [ 2094-72-6 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 2094-72-6 ]

CAS No. :	2094-72-6	MDL No. :	MFCD00074724
Formula :	C₁₁H₁₅ClO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MIBQYWIOHFTKHD-UHFFFAOYSA-N
M.W :	198.69	Pubchem ID :	98915
Synonyms :

Safety of [ 2094-72-6 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	3261
Hazard Statements:	H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 2094-72-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 2094-72-6 ]
Downstream synthetic route of [ 2094-72-6 ]

[ 2094-72-6 ] Synthesis Path-Upstream 1~5

1
[ 186581-53-3 ]
[ 2094-72-6 ]
[ 4942-47-6 ]

Reference： [1] Chemische Berichte, 1959, vol. 92, p. 1629,1632

2
[ 186581-53-3 ]
[ 2094-72-6 ]
[ 5122-82-7 ]

Reference： [1] Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, # 11, p. 2058 - 2062[2] Zhurnal Organicheskoi Khimii, 1986, vol. 22, # 11, p. 2292 - 2296

3
[ 2094-72-6 ]
[ 40430-66-8 ]

Reference： [1] Journal of the American Chemical Society, 1978, vol. 100, p. 4852 - 4858

4
[ 2094-72-6 ]
[ 5511-18-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With ammonia In water at 20℃; for 2 h;	To a stirred mixture of 1-adamantanecarboxylic acid (11, 36.05 g, 200 mmol) and DMF (5 drops)in CH2Cl2 (360 mL) cooled in an ice-water bath was added thionyl chloride (26.17 g, 220 mmol) inone portion. The resulting mixture was refluxed until the evolution of HCl gas ceased (typicallywithin 2 h). The solvent and excess thionyl chloride were then removed on a rotary evaporator, andthe crude acid chloride 12 was dissolved in THF (100 mL). The resulting solution was then slowlyadded dropwise to stirred concentrated aqueous ammonia (400 mL) cooled in an ice-water bath.After addition, the resulting white slurry was stirred at room temperature for another 2 h, and thewhite precipitates were collected via vacuum filtration, washed with cold n-hexane and dried invacuo to afford 1-adamantanecarboxamide (13). White solid; 34.06 g (95percent); m.p. 177–179 °C(literature value, 185.5–191.7 °C [48]). 1H-NMR (DMSO-d6, 400 MHz) δ: 6.89 (brs, 1H), 6.62 (brs, 1H),1.93 (s, 3H), 1.73–1.74 (m, 6H), 1.60–1.68 (m, 6H).

Reference： [1] Molecules, 2018, vol. 23, # 2,
[2] Chemistry - A European Journal, 2016, vol. 22, # 15, p. 5156 - 5159
[3] Synthetic Communications, 1988, vol. 18, # 11, p. 1179 - 1186
[4] Journal of Organic Chemistry, 1981, vol. 46, # 20, p. 3988 - 3991
[5] Chemische Berichte, 1960, vol. 93, p. 226 - 230
[6] Pharmaceutical Chemistry Journal, 1987, vol. 21, # 4, p. 287 - 291[7] Khimiko-Farmatsevticheskii Zhurnal, 1987, vol. 21, # 4, p. 454 - 458
[8] Chemical Communications, 1998, # 21, p. 2297 - 2298
[9] Russian Journal of General Chemistry, 1999, vol. 69, # 11, p. 1844 - 1845[10] Zhurnal Obshchei Khimii, 1999, vol. 69, # 11, p. 1927 - 1928
[11] Patent: WO2008/64432, 2008, A1, . Location in patent: Page/Page column 57; 61
[12] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 13, p. 3720 - 3723
[13] Patent: WO2008/106128, 2008, A2, . Location in patent: Page/Page column 27-28

5
[ 120-72-9 ]
[ 2094-72-6 ]
[ 1097119-35-1 ]

Reference： [1] Journal of Organic Chemistry, 2011, vol. 76, # 11, p. 4753 - 4758
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 1, p. 295 - 315

[ 2094-72-6 ] Synthesis Path-Downstream 1~88

1
[ 29927-08-0 ]
[ 2094-72-6 ]
[ 35871-28-4 ]

Reference： [1]Journal of medicinal chemistry,1971,vol. 14,p. 1222 - 1223

2
[ 13330-96-6 ]
[ 2094-72-6 ]
Adamantane-2-carboxylic acid 4-dimethylamino-butyl ester [ No CAS ]

Reference： [1]Pharmaceutical Chemistry Journal,1979,vol. 13,p. 710 - 713
Khimiko-Farmatsevticheskii Zhurnal,1979,vol. 13,p. 41 - 45

3
[ 2094-72-6 ]
[ 770-71-8 ]

Reference： [1]Journal of medicinal chemistry,1967,vol. 10,p. 517 - 521
[2]Synthetic Communications,1989,vol. 19,p. 387 - 392

4
[ 2094-72-6 ]
[ 5511-18-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With ammonia; In water; at 20℃; for 2h;	To a stirred mixture of 1-adamantanecarboxylic acid (11, 36.05 g, 200 mmol) and DMF (5 drops)in CH2Cl2 (360 mL) cooled in an ice-water bath was added thionyl chloride (26.17 g, 220 mmol) inone portion. The resulting mixture was refluxed until the evolution of HCl gas ceased (typicallywithin 2 h). The solvent and excess thionyl chloride were then removed on a rotary evaporator, andthe crude acid chloride 12 was dissolved in THF (100 mL). The resulting solution was then slowlyadded dropwise to stirred concentrated aqueous ammonia (400 mL) cooled in an ice-water bath.After addition, the resulting white slurry was stirred at room temperature for another 2 h, and thewhite precipitates were collected via vacuum filtration, washed with cold n-hexane and dried invacuo to afford 1-adamantanecarboxamide (13). White solid; 34.06 g (95%); m.p. 177-179 C(literature value, 185.5-191.7 C [48]). 1H-NMR (DMSO-d6, 400 MHz) delta: 6.89 (brs, 1H), 6.62 (brs, 1H),1.93 (s, 3H), 1.73-1.74 (m, 6H), 1.60-1.68 (m, 6H).
	With ammonia; In tetrahydrofuran; water; at 20℃; for 1h;	1-Adamantanecarboxylic acid (7.4 g, 41 mmol) was heated to reflux with thionyl chloride (15 mL) and DMF (2 drops) for 3 h. The excess thionyl chloride was distilled off under reduced pressure, and the residual traces were removed in vacuo for 15 min. The residue was dissolved in THF (20 mL) and added to aq. NH3 (100 mL, 30%) with ice cooling and stirring. After stirring for 1 h at room temperature, the precipitate was filtered off, H2O (ca. 1 L) added, followed by CH2Cl2 (ca. 200 mL) until the entire solid dissolved. The organic layer was collected, dried (Na2SO^) and evaporated in vacuo for 5 h to give 1-adamantanecarboxamide (5.15 g) as a colourless solid; 1H NMR (200 MHz, CDCl3) S 5.75 (br), 2.05 (3H, br s), 1.89-1.88 (6H, m), 1.80-1.63 (6H, m).
	With ammonia; In tetrahydrofuran; water; at 0 - 20℃; for 2h;Alkaline aqueous solution;	Adamantane-1-carboxyliotac acid (10 g, 55 mmol) was heated at reflux with thionyl chloride (15 mL) and dimethylformamide (1 drop) for 2 h under an inert atmosphere <n="29"/>Excess thionyl chloride was distilled off under vacuum. The residue was dissolved in THF (30 mL) and added to a solution of concentrated aqueous ammonia (135 ml_) at 0 0C. The reaction was stirred for 2 h at rt. The mixture was cooled to 10 0C and filtered to give the crude product, which was washed with water and dried to afford admantane-1-carboxamide (6.6 g, 67%). 1H NMR (CDCI3, 400 MHZ): delta=1.71-2.04 (t, 15H), 5.66-5.75 (d, 2H).

Reference： [1]Molecules,2018,vol. 23
[2]Chemistry - A European Journal,2016,vol. 22,p. 5156 - 5159
[3]Synthetic Communications,1988,vol. 18,p. 1179 - 1186
[4]Journal of Organic Chemistry,1981,vol. 46,p. 3988 - 3991
[5]Chemische Berichte,1960,vol. 93,p. 226 - 230
[6]Pharmaceutical Chemistry Journal,1987,vol. 21,p. 287 - 291
Khimiko-Farmatsevticheskii Zhurnal,1987,vol. 21,p. 454 - 458
[7]Chemical Communications,1998,p. 2297 - 2298
[8]Russian Journal of General Chemistry,1999,vol. 69,p. 1844 - 1845
Zhurnal Obshchei Khimii,1999,vol. 69,p. 1927 - 1928
[9]Patent: WO2008/64432,2008,A1 .Location in patent: Page/Page column 57; 61
[10]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 3720 - 3723
[11]Patent: WO2008/106128,2008,A2 .Location in patent: Page/Page column 27-28

5
[ 67-56-1 ]
[ 2094-72-6 ]
[ 711-01-3 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 7162 - 7167
[2]Journal of the Chemical Society. Perkin transactions II,1996,p. 1811 - 1820
[3]Journal of Chemical Thermodynamics,1992,vol. 24,p. 1299 - 1304

6
[ 770-71-8 ]
[ 2094-72-6 ]
[ 78679-70-6 ]

Reference： [1]Tetrahedron Letters,1985,vol. 26,p. 661 - 664
[2]Tetrahedron,1987,vol. 43,p. 701 - 710
[3]Croatica Chemica Acta,2009,vol. 82,p. 833 - 839

7
[ 57497-39-9 ]
[ 2094-72-6 ]
N-tert-Butyl-O-(1-adamantancarbonyl)hydroxylamin [ No CAS ]
N-tert-Butyl-1-adamantancarbohydroxamsaeure [ No CAS ]

Reference： [1]Archiv der Pharmazie,1986,vol. 319,p. 1037 - 1043

8
[ 2094-72-6 ]
[ 15898-47-2 ]
[ 123796-91-8 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1988,vol. 27,p. 1125 - 1127

9
[ 2094-72-6 ]
[ 131211-27-3 ]
Di-1-adamantyl-(1-adamantoyl)phosphin [ No CAS ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,1993,vol. 85,p. 193 - 206

10
[ 39684-28-1 ]
[ 2094-72-6 ]
[ 168139-37-5 ]

Reference： [1]Journal of the American Chemical Society,1995,vol. 117,p. 4870 - 4874
[2]Journal of the Chemical Society. Perkin Transactions 2 (2001),2002,p. 1728 - 1739

11
[ 15031-77-3 ]
[ 2094-72-6 ]
2-(3-Pyridyl)propan-2-yl 1-adamantanecarboxylate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 3319 - 3323

12
[ 50392-78-4 ]
[ 2094-72-6 ]
(R,S)-1-(4-pyridyl)ethyl 1-adamantanecarboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 3319 - 3323

13
[ 2094-72-6 ]
[ 27854-88-2 ]
(+)-(R)-1-(4-Pyridyl)ethyl 1-adamantanecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; In tetrahydrofuran; hexane;	EXAMPLE 2 (+)-(R)-1-(4-Pyridyl)ethyl 1-adamantanecarboxylate The method followed that described in Example 1, but using (+)-(R)-1-(4-pyridyl)ethanol (369 mg, 3.0 mmol) in THF (12 ml), n-butyllithium (2.5 M, 1.2 ml, 3.0 mmol) in hexane, and 1-adamantanecarbonyl chloride (656 mg, 3.3 mmol) in THF (3 ml). Chromatography, on elution with petrol-ether-triethylamine 200:50:1, afforded the title compound (754 mg, 88%). [alpha]D +25.8 (c 1, CHCl3); IR numax 1730 cm-1; 1 H-NMR (CDCl3) delta1.50 (3H, d, J 6.6 Hz, CHCH3), 1.73 and 1.93 (12H, 2s, adamantyl CH2), 2.04 (3H, s, adamantyl CH), 5.80 (1H, q, J 6.6 Hz, OCH), 7.23 (2H, d, J 6.1 Hz, Py 3 and 5H), 8.58 (2H, d, J 6.1 Hz, Py 2 and 6H); MS m/z 285 (M+). By passing hydrogen chloride gas through a solution of the product in ether, the hydrochloride was obtained, m.p. 164-166 C. Anal. Calcd: C, 67.17; H, 7.52; N, 4.35. Found: C, 67.58; H, 7.51; N, 4.36%.

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 3319 - 3323
[2]Patent: US5595995,1997,A

14
[ 2094-72-6 ]
[ 27854-96-2 ]
(S)-(-)-1-(4-pyridyl)ethyl 1-adamantanecarboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 3319 - 3323

15
[ 2094-72-6 ]
[ 2735-62-8 ]
3-Adamantan-1-yl-2-(1-methyl-1H-benzoimidazol-2-yl)-3-oxo-propionitrile [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1997,vol. 33,p. 445 - 447

16
[ 20603-00-3 ]
[ 2094-72-6 ]
2-(hexahydro-1H-azepin-1-yl)ethyl 1-adamantylethanoate hydrochloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 3244 - 3253

17
[ 6240-11-5 ]
[ 2094-72-6 ]
adamantane-1-carboxylic acid 2-adamantan-1-yl-ethyl ester [ No CAS ]

Reference： [1]Russian Journal of Applied Chemistry,2003,vol. 76,p. 105 - 107

18
[ 57009-12-8 ]
[ 2094-72-6 ]
[ 750572-54-4 ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4268 - 4276

19
[ 1454-85-9 ]
[ 2094-72-6 ]
1-heptadecyl 1-adamantanecarboxylate [ No CAS ]

Reference： [1]Russian Journal of Organic Chemistry,2004,vol. 40,p. 346 - 352

20
[ 98-55-5 ]
[ 2094-72-6 ]
dimethyl(4-methyl-3-cyclohexenyl)methyl 1-adamantanecarboxylate [ No CAS ]

Reference： [1]Russian Journal of Organic Chemistry,2004,vol. 40,p. 346 - 352

21
[ 53297-68-0 ]
[ 2094-72-6 ]
adamantane-1-carboxylic acid (2-chloro-4-sulfamoyl-phenyl)-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2717 - 2726

22
[ 2094-72-6 ]
[ 138-37-4 ]
4-(1-adamantylcarboxamidomethyl)benzenesulfonamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2717 - 2726

23
[ 29390-67-8 ]
[ 2094-72-6 ]
mono-6-deoxy-6-(1-adamantylcarboxamido)-β-cyclodextrin [ No CAS ]

Reference： [1]Acta Crystallographica Section B: Structural Science,2004,vol. 60,p. 204 - 210

24
[ 2094-72-6 ]
[ 83558-87-6 ]
5,5'-(hexafluoroisopropylidene)bis(2-hydroxyadamantanecarboanilide) [ No CAS ]

Reference： [1]Macromolecules,2004,vol. 37,p. 8256 - 8261

25
[ 61296-22-8 ]
[ 2094-72-6 ]
[ 959600-22-7 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;dmap; In tetrahydrofuran; at 80℃; for 48h;	A mixture of <strong>[61296-22-8]2-amino-5-bromothiazole monohydrobromide</strong> (3.00 g, 11 ,5 mmol), 1-adamanianecarbonyl chloride (2.74 g, 13 8 mmol), A- dimethylaminopyridine (LlO g, 0,90 mmol) and triethylamine (3.20 mL, 23.0 mmol) in 100 mL of THF was stirred at 80 0C for 48 hours The mixture was cooled to ambient temperature, diluted with 100 mL of ethyl acetate and washed with brine. <n="44"/>The layers were separated and the aqueous phase was extracted with 2 X 50 mL ethyl acetate The combined organic extracts were dried over anhydrous Na2SOd, filtered, and concentrated Purification by column chromatography (SiOi, 20% ethyl acetate: 80% hexane) afforded 2 55 g of the title compound 1H NMR {400 MHz, DMSO-(Z6) delta 1 67 - 1 72 (m, 6 H) 1 92 (d, ./=2 8 Hz, 6 H) 1 97 - 2 04 (m, 3 H) 7 55 (s, 1 H) 1 1 50 (br m, 1 H); MS (DCI/NH3) m/z 341 (M)+, 343 (M+2)+

Reference： [1]Patent: WO2007/140439,2007,A2 .Location in patent: Page/Page column 42-43p; 65-66

26
[ 2289-75-0 ]
[ 2094-72-6 ]
adamantane-1-carboxylic acid {4,5-dimethyl-3-[2-(2,2,2-trifluoro-ethoxy)-ethyl]-3H-thiazol-2-ylidene}-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		4,5-Dimeiotahyl~thiazol-2-ylamine and 2-(2-bromo-ethoxy)-l )l,l-trifiuoio- ethane were mixed and heated at 65 0C foi 4 hours The iesidue was triturated with hexane to affoid the title compound MS (ESI+) m/z 255 (M+eta)+; To a solution of Example 85 A (0 20 g, 0 8 mmol) in TetaF (10 mL) was added triethylamine (0 4 mL) and adamantane-1-caibonyl chloride (0 2 g, 1 mmol). The mixture was heated at ieflux overnight and then concentrated under reduced pressure The residue was diluted with ethyl acetate, washed with IM aqueous NaHCO3, dried (Na2SO1S), filtered, and concentrated Purification by preparative etaPLC on a Waters Symmetry C8 column (40 mm X 100 mm, 7 mum particle size) using a gradient of 10 % to 100 % acetonitrile: ammonium acetate (10 mM) over 15 minutes at a flow rate of 70 mL/minutes afforded 10 mg of the title compound 1H NMR (300 MHz, DMSO- d6) delta ppm 1 60 - 1.75 (m, J=28 8 Hz, 6 H), 1.83 (d, J=2.7 Hz, 6 H), 1 93 - 2 01 (m, 3 H), 2 15 (s, 3 H), 2.20 (s, 3 H), 3 92 (t, J=5.3 Hz, 2 H), 4 09 (q, J-9.5 Hz, 2 H), 4,28 (t, >5.3 Hz, 2 H); MS (ESI+) m/z 417 (M+H)+; Anal Calculated for C20Hi7F3N2O2S: C, 57.67; H, 6 53; N, 6 73. Found: C, 57 53; H, 6 55; N, 6 69,

Reference： [1]Patent: WO2007/140439,2007,A2 .Location in patent: Page/Page column 78

27
[ 71574-33-9 ]
[ 2094-72-6 ]
[ 377063-72-4 ]

Yield	Reaction Conditions	Operation in experiment
74%		To a solution of 4,5~dimethyl-ihiazo3-2-ylamine hydrochloride (1 65 g, 10 0 mmol) in TetaF (100 mL) was added tiiethylamine (4 2 mL, 30 mmol) and adamantane-l-carbonyl chloride (2 2 g, 1 1 mmol) The mixture was heated at reflux overnight and then concentrated under reduced pressure The residue was diluted with ethyl acetate, washed with IM NaHCO3, dried (Na2SO4), filtered and concentrated Purification by column chromatography (SiO2, 10 %ethyl acetate: 90% hexanes) afforded 2 15 g (74%) of the title compound MS (ESI+) m/z 291 (M+H)+

Reference： [1]Patent: WO2007/140439,2007,A2 .Location in patent: Page/Page column 83

28
[ 3034-22-8 ]
[ 2094-72-6 ]
[ 959600-22-7 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;dmap; In tetrahydrofuran; at 80℃; for 48h;	A mixture of 5-bromothiazol-2-amine (3 Og, 1 1 5 mmol), adamantane-1 - carbonyl chloride (2 74 g, 13 8 mmol), tiiethylamine (3 2 mL, 23 mmol) and 4- di(methylamino)pyridine (1.1 g) in tetrahydrofuran ( 100 mL) was heated at 80 0C for 48 hours The mixture was cooled to ambient temperature1, concentrated, diluted with water and extracted with ethyl acetate The organic extract was dried (Na2SO4), filtered and concentrated Purification by flash chromatography (silica gel, 25percent ethyl acetate /hexanes) afforded the title compound. MS (ESI) m/z 342 (M+H)"1

Reference： [1]Patent: WO2007/140439,2007,A2 .Location in patent: Page/Page column 101

29
[ 2094-72-6 ]
[ 75-26-3 ]
C₂₅H₃₈O₂ [ No CAS ]
[ 770-71-8 ]
[ 78679-70-6 ]
α-isopropyl-1-adamantemethanol [ No CAS ]

Reference： [1]Collection of Czechoslovak Chemical Communications,2006,vol. 71,p. 709 - 722

30
[ 2094-72-6 ]
aminoacyl chlorotrityl resin [ No CAS ]
[ 5511-18-2 ]

Reference： [1]Synthesis,2001,p. 914 - 918

31
[ 2094-72-6 ]
[ 40430-66-8 ]

Reference： [1]Journal of the American Chemical Society,1978,vol. 100,p. 4852 - 4858

32
[ 2094-72-6 ]
[ 32854-09-4 ]
N,N-diadamantylcarbonyl-L-cystine methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With triethylamine;	Due to the versatility with which adamantyl amide analogues can be synthesized by combining the commercially available 1-adamantylcarbonyl chloride with amino-acid methyl and ethyl esters, a series of adamantyl amnide analogues was synthesized. The resulting methyl and ethyl esters in all but one case were readily converted to the corresponding acids by saponification with lithium hydroxide as shown in (Scheme30).

Reference： [1]Patent: US2004/242542,2004,A1 .Location in patent: Page/Page column 6-8

33
[ 2094-72-6 ]
[ 13515-95-2 ]
[ 313269-35-1 ]

Yield	Reaction Conditions	Operation in experiment
55%	With triethylamine;	Due to the versatility with which adamantyl amide analogues can be synthesized by combining the commercially available 1-adamantylcarbonyl chloride with amino-acid methyl and ethyl esters, a series of adamantyl amnide analogues was synthesized. The resulting methyl and ethyl esters in all but one case were readily converted to the corresponding acids by saponification with lithium hydroxide as shown in (Scheme30).

Reference： [1]Patent: US2004/242542,2004,A1 .Location in patent: Page/Page column 6-7

34
[ 2094-72-6 ]
[ 26081-03-8 ]
[ 876064-02-7 ]

Yield	Reaction Conditions	Operation in experiment
59%	With sodium carbonate; In dichloromethane; water; at 20℃; for 2.0h;	Example 6: (5)-3-(l '-Adamantanecarbonyl)amino-caprolactam:(>S)-3-amino-caprolactam hydrochloride 2 (1 mmol) and Na2C03 (3 mmol) in water (15 ml) were added to a solution of 1-adamantanecarbonyl chloride (1 mmol) in dichloromethane (15 ml) at ambient temperature and the reaction was stirred for 2 hours. The organic layer was then separated and the aqueous phase was extracted with additional dichloromethane (2 x 25 ml). The combined organic layers were dried over Na2C03 and reduced in vacuo. The residue was recrystallised from CH2C12 / hexanes to give (S)-3-(l '-adamantanecarbonyl)amino-caprolactam (171 mg, 59%); m.p. 256-258 C; [a]f (c = 1, CHC13) +29.5; vjcm'1 3411, 3259 (NH), 1678, 1626 (CO), 1505 (NH); 5H (500 MHz, CDC13) 7.08 (1H, d, J5.5, CHNH), 6.67 (1H, br s, CH2NNo.), 4.47 (1H, ddd, J11, 5.5, 1.5, CHNH), 3.32-3.17 (2H, m, CNo.2NH), 2.06-1.94 (5H, m, 2 x ring CH + 3 x adamantane CH), 1.90-1.75 (8H, m, 2 x ring CH + 3 x adamantane CH2), 1.72 (3H, br d, J 14.5, 3 x adamantane CHH), 1.68 (3H, br d, J 14.5, 3 x adamantane CHH) and 1.47-1.32 (2H, m, 2 x ring CH); 5C (125 MHz, CDC13) 177.2, 175.9 (CO), 51.9 (NHCHCO), 42.2 (CH2N), 40.5 (CCO), 39.0 (3 x CH2 adamantane), 36.5 (3 x CH2 adamantane), 31.7, 28.9, 28.0 (CH2 lactam), 28.1 (3 x CH adamantane); m/z (MH4 C17H27N202 requires 291.2073) 291.1994.

Reference： [1]Patent: WO2006/16152,2006,A1 .Location in patent: Page/Page column 16-17
[2]Journal of Medicinal Chemistry,2009,vol. 52,p. 3591 - 3595

35
[ 635-26-7 ]
[ 2094-72-6 ]
[ 912963-26-9 ]

Yield	Reaction Conditions	Operation in experiment
77%	With triethylamine; In tetrahydrofuran; at 20℃; for 2h;	Example 1 A^-(2-methylphenyl)adamantane- 1 -carbohydrazide; To an oven-dried, 25-mL, round-bottomed flask containing a magnetic stir bar was added the hydrochloride salt of o-tolylhydrazine (174 mg, 1.10 mmol). The flask was sealed with a septum and purged with nitrogen atmosphere. Anhydrous tetrahydrofuran (9 niL) was added via syringe to form a white slurry. Triethylamine (419 muL, 3.00 mmol) was added via syringe. A solution of 1-chlorocarbonyl adamantane (199 mg, 1.00 mmol) in anhydrous tetrahydrofuran (1 niL) was added. The white slurry was stirred at room temperature for 2 hours and then monitored by LC-MS (Hewlett-Packard 1100 HPLC with a Finnigan EPO <DP n="22"/>Navigator MS; C18 reverse phase column; 10-100% acetonitrile:10 mM ammonium acetate gradient; APCI positivie ionization) Water (10 mL) was added to quench and the reaction mixture was transferred to a separatory funnel. The mixture was extracted with dichloromethane (3 x 8 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated by rotary evaporator to give an off-white solid. The product was re-crystallized from ethyl acetate/hexanes to give 220 mg (77%) of a white powder. MS (ESI+) m/z 285.1 (M+H)+; 1HNMR (CDCl3) delta 1.72-1.81 (m, 6H), 1.95-1.96 (m, 6H), 2.09 (br s, 3H), 2.26 (s, 3H), 3.60 (br s, IH), 6.78-6.86 (m, 2H), 7.06-7.13 (m, 2H), 7.38 (br s, IH). Anal. Calc'd for C18H24N2O: C, 76.02; H, 8.51; N, 9.85. Found: C, 75.72; H, 8.73; N, 9.75.

Reference： [1]Patent: WO2006/110516,2006,A1 .Location in patent: Page/Page column 20
[2]Journal of Medicinal Chemistry,2008,vol. 51,p. 3030 - 3034

36
[ 54903-50-3 ]
[ 2094-72-6 ]
[ 911056-85-4 ]

Yield	Reaction Conditions	Operation in experiment
33%		Adamantan-l-yI-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)-methanone (STX1721, XDS04025);To a solution of 1-adamantanecarbonyl chloride (lOOmg, 0.50 mmol, 1.06 eq.) in DCM (5 mL) was added triethylamine (0.15 mL), followed by the 4,5,6,7-Tetrahydrothieno[3,2- c]pyridine (155mg, purity unknown). The reaction mixture was stirred at ambient temperature under nitrogen overnight. PS-Trisamine (10-20 mg) was added. After stirred at ambient temperature for another 2h, the mixture was filtered and evaporation of the solvent gave a residue that was purified by flash chromatography (Hexane-Ethyl acetate/hexane gradient elution) to give crystalline solid (49 mg, 33 %). mp 141-143 0C; TLC single spot at Rf. 0.49 (20% ethyl acetate/hexane); 1H NMR (270 MHz3 CDCl3) delta 1.72 (6H, s, 3 x CH2), 2.02 (9H, s, 3 x CH and 3 x CH2), 2.88 (2H, t, J= 4.6 Hz5 CH2), 3.94 (2H, t, J= 4.5 Hz, CH2), 4.69 (2H, s, CH2), 6.79 (IH, d, J= 5.2 Hz, ArH) and 7.11 (IH, d, J= 5.2 Hz3 ArH); LC/MS (APCI) m/z 302 (M÷+H); HPLC tr = 3.24 min (>99 %) in 10% water-acetonitrile.

Reference： [1]Patent: WO2006/100502,2006,A1 .Location in patent: Page/Page column 118

37
[ 2094-72-6 ]
[ 56973-26-3 ]
[ 66148-57-0 ]

Yield	Reaction Conditions	Operation in experiment
	In pyridine; water; ethyl acetate;	EXAMPLE 5 To a solution of 1-adamantanecarbonylchloride (39.73 g) in pyridine (260 ml) was added 4-carbamoylimidazolium-5-olate (12.71 g) and the reaction temperature was maintained at 41-43 C. for 3.5 hours. Pyridine was removed under reduced pressure. To the residue was added ethylacetate (300 ml) and water (300 ml), and stirred at room temperature for 1 hour. The insoluble solid was filtered and washed with ethyl acetate to give almost pure 5-carbamoyl-1H-imidazol-4-yl 1-adamantanecarboxylate (25.9 g, beta form, m.p. 205-205.5 C. (dec.)). Recrystallization from dimethylformamide-diethylether gave analytically pure sample (beta form m.p. 213.5-216.5 C. (dec.)).
	With triethylamine; In N-methyl-acetamide; water; ethyl acetate;	EXAMPLE 6 To a suspension of 4-carbamoylimidazolium-5-olate (1.016 g) in dimethylformamide (20 ml) was added triethylamine (1.942 g) at 0-5 C. and then 1-adamantanecarbonylchloride (3.50 g) in dimethylformamide (20 ml) dropwisely over 24 minutes. The reaction mixture was stirred at 0-5 C. for 23 hours. The solvent was removed under reduced pressure. To the residue was added ethyl acetate (20 ml) and water (20 ml), and stirred at room temperature for 1 hour. The insoluble solid was filtered and washed with ethyl acetate to give almost pure 5-carbamoyl-1H-imidazol-4-yl 1-adamantanecarboxylate (1.5 g, alpha form, m.p. 206.5-207.5 C. (dec.)), which was washed thoroughly with ethyl acetate to give pure product, alpha form, m.p. 211 C. (dec.).
	With triethylamine; In N-methyl-acetamide; water; ethyl acetate;	EXAMPLE 9 To a suspension of 4-carbamoylimidazolium-5-olate (4.064 g) in dimethylformamide (80 ml) was added triethylamine (7.768 g) at 0-5 C. and then 1-adamantanecarbonylchloride (14.00 g) in dimethylformamide (80 ml) dropwisely over 22 minutes. The reaction mixture was stirred at 0-5 C. for 15 hours. The solvent was removed under reduced pressure. To the residue was added ethyl acetate (100 ml) and water (100 ml), and stirred at room temperature for 1 hours. The insoluble solid was filtered and washed with ethyl acetate to give almost pure 5-carbamoyl-1H-imidazol-4-yl 1-adamantanecarboxylate (5.67 g, beta form, m.p. 207-210 C. (dec.)).

In pyridine; water; ethyl acetate;

EXAMPLE 7 To a solution of 1-adamantanecarbonylchloride (2.980 g) in pyridine (26 ml) was added 4-carbamoylimidazolium-5-olate (1.271 g) and the reaction temperature was kept at 40-43 C. for 4 hours. Unreacted starting material was recovered by filtration (210 mg). The filtrate was concentrated under reduced pressure. To the residue was added ethyl acetate (30 ml) and water (30 ml), and stirred at room temperature for 1 hour. The insoluble solid was filtered and washed with ethyl acetate to give almost pure 5-carbamoyl-1H-imidazol-4-yl 1-adamantanecarboxylate (1.602 g, alpha form, m.p. 207-209 C. (dec.)).

Reference： [1]Patent: US4260774,1981,A
[2]Patent: US4260774,1981,A
[3]Patent: US4260774,1981,A
[4]Patent: US4260774,1981,A

38
[ 54745-74-3 ]
[ 2094-72-6 ]
[ 60626-59-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In diethyl ether; water; Petroleum ether;	EXAMPLE 31 3-(1-Adamantanecarbonyl)-8-Oxa-3-Azabicyclo(3.2.1)Octane SPC10 1-Adamantanecarbonyl chloride (19.87 grams, 0.1 mole, pulverized) (Aldrich Chemical Co., Inc., Milwaukee, Wisc.) was added to a mixture of 8-oxa-3-azabicyclo(3.2.1)octane hydrochloride (14.96 grams, 0.1 mole) and sodium hydroxide (10 grams) in 300 ml water. The reaction mixture was heated at 30 C. for 3 hours and then left overnight at room temperature. The product (22 grams) was filtered off, washed with water, and finally recrystallized from a blend of about 30% petroleum ether (boiling point 30-60 C.) and 70% diethyl ether (v/v). The product had a melting point of 134-136 C. Analysis for C17 H25 NO2. Calculated: C, 74.14%; H, 9.15%; N, 5.08%. Found: C, 74.10%; H, 9.21%; N, 5.06%.

Reference： [1]Patent: US3953596,1976,A

39
[ 2094-72-6 ]
[ 42538-31-8 ]
(S)-3-(1'-adamantanecarbonylamino)-tetrahydropyridin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With sodium carbonate; In dichloromethane; water; at 20℃; for 18h;	Example 1: - (S)-3-(l'-Adamantanecarbonylamino)-tetrahydropyridin-2-one:; ()S)-3-Amino-tetrahydropyridin-2-one hydrochloride (2 mmol) and Na2CO3 (6 mmol) in water (25 ml) were added to a solution of adamantane-1-carbonyl chloride (2 mmol) in dichloromethane (25 ml) at ambient temperature and the reaction was stirred for 18 hours. The organic layer was then separated and the aqueous phase was extracted with additional dichloromethane. The combined organic layers were dried over Na2SO4 and reduced in vacuo. The residue was recrystallised from CH2Cl2 / hexanes to give the lactam as an amorphous solid (237 mg, 43%); vmjcm l 3330, 3175 (NH), 1655, 1683 (CO), 1500 (NH); deltaH (400 MHz, CDCl3) 6.59 (IH, br d, J4.5, NH), 6.51 (IH, br s, NH), 4.15 (IH, dt, J lO, 5.5, CHNH), 3.35-3.24 (2H, m, CH2NH), 2.57-2.48 (IH, m, lactam CH2), 1.99 (3H, br s, 3 x adamantane CH), 1.92-1.17 (8H, m, 2 x lactam CH and 6 x adamantane CH2), 1.73-1.61 (6H, m, 6 x adamantane CH2) and 1.45 (IH, tt, J 12.5, 8.5, lactam CH); deltac (100 MHz, CDCl3) 178.2, 172.2 (CO), 50.3 (NHCHCO), 41.5 (CH2N), 40.6 (CCO), 39.1 (3 x CH2 adamantane), 36.5 (3 x CH2 adamantane), 28.1 (3 x CH adamantane), 27.0, 21.0 (CH2 lactam); m/z (MNa+ C16H24N2O2Na requires 299.1735), 299.1739, (MH+ C16H25N2O2 requires 277.1916) 277.1919.

Reference： [1]Patent: WO2006/134385,2006,A2 .Location in patent: Page/Page column 14

40
[ 2924-16-5 ]
[ 2094-72-6 ]
[ 912963-99-6 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 3030 - 3034

41
[ 21938-47-6 ]
[ 2094-72-6 ]
[ 912963-89-4 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 3030 - 3034

42
[ 2094-72-6 ]
[ 51169-05-2 ]
[ 1029433-07-5 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 3030 - 3034

43
[ 2094-72-6 ]
[ 56737-78-1 ]
[ 912963-96-3 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 3030 - 3034

44
[ 42270-37-1 ]
[ 2094-72-6 ]
[ 1043138-52-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 3209 - 3213

45
[ 39115-94-1 ]
[ 2094-72-6 ]
[ 332037-13-5 ]

Yield	Reaction Conditions	Operation in experiment
27%	With triethylamine; In dichloromethane; at 0℃; for 3h;	A solution of 1 -admantanecarbonyl chloride ( 1 .6 g, 8 mmol) in dichloride (5 mL) was added dropwise to a solution of <strong>[39115-94-1]3-iodobenzohydrazide</strong>(2.0 g, 7.6 mmol) and triethylamine (1.0 g, 10 mmol) in dichloride ( 15 mL) at 0C with stirring. After stirring for an additional 3h at 0C, saturated ammonium chloride (30 mL) was poured into the mixture, and the organic layer was separated and washed subsequently with saturated sodium biscarbonate aqueous solution (30 mL), water (30 mL) and dried over anhydrous sodium sulfate. Upon removal of sodium sulfate by filtration and solvent under reduced pressure, the resulting residue was rinsed with ether to give a white solid 980 mg. Yield: 27%. (300MHz, CDC13): delta 10.4(s, 1 H), 8.6(s, 1 H), 8.35-8.34(m, 1 H), 8.04-8.00(m, 1 H), 7.85-7.81 (m, 1 H), 7.26-7.19(m, 1 H), 1.9 (s, 2H), 1.68-1.54(m, 13H). EI-MS (m/z): M+ calcd for C18H21 I 2O2, 424.28; found 425.1.

Reference： [1]Patent: WO2012/88316,2012,A1 .Location in patent: Page/Page column 49-51

46
[ 69807-81-4 ]
[ 2094-72-6 ]
[ 911055-89-5 ]

Yield	Reaction Conditions	Operation in experiment
76%	With triethylamine; In dichloromethane; at 20℃;Inert atmosphere;	General procedure: To a solution of the 1-adamantane carbonyl chloride (0.50 mmol, 1.06 equiv) in DCM (5 mL) was added triethylamine (0.15 mL), followed by the corresponding amine (0.47 mmol, 1 equiv). The reaction mixture was stirred at ambient temperature under nitrogen overnight. PS-Trisamine (10-20 mg) was added. After stirring at ambient temperature for another 2 h, the mixture was filtered and evaporation of the solvent gave a residue that was purified by flash chromatography (ethyl acetate-DCM gradient elution) to give the desired carboxamide derivatives.

Reference： [1]Bioorganic and medicinal chemistry,2012,vol. 20,p. 6394 - 6402,9

47
[ 2094-72-6 ]
[ 18759-96-1 ]
[ 1401415-90-4 ]

Yield	Reaction Conditions	Operation in experiment
88%	With triethylamine; In dichloromethane; at 20℃;Inert atmosphere;	General procedure: To a solution of the 1-adamantane carbonyl chloride (0.50 mmol, 1.06 equiv) in DCM (5 mL) was added triethylamine (0.15 mL), followed by the corresponding amine (0.47 mmol, 1 equiv). The reaction mixture was stirred at ambient temperature under nitrogen overnight. PS-Trisamine (10-20 mg) was added. After stirring at ambient temperature for another 2 h, the mixture was filtered and evaporation of the solvent gave a residue that was purified by flash chromatography (ethyl acetate-DCM gradient elution) to give the desired carboxamide derivatives.

Reference： [1]Bioorganic and medicinal chemistry,2012,vol. 20,p. 6394 - 6402,9

48
[ 39191-07-6 ]
[ 2094-72-6 ]
N-(4-chlorobenzyl)-N-methyladamantane-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With triethylamine; In dichloromethane; at 20℃;Inert atmosphere;	General procedure: To a solution of the 1-adamantane carbonyl chloride (0.50 mmol, 1.06 equiv) in DCM (5 mL) was added triethylamine (0.15 mL), followed by the corresponding amine (0.47 mmol, 1 equiv). The reaction mixture was stirred at ambient temperature under nitrogen overnight. PS-Trisamine (10-20 mg) was added. After stirring at ambient temperature for another 2 h, the mixture was filtered and evaporation of the solvent gave a residue that was purified by flash chromatography (ethyl acetate-DCM gradient elution) to give the desired carboxamide derivatives.

Reference： [1]Bioorganic and medicinal chemistry,2012,vol. 20,p. 6394 - 6402,9

49
[ 20173-04-0 ]
[ 2094-72-6 ]
[ 911057-52-8 ]

Yield	Reaction Conditions	Operation in experiment
91%	With triethylamine; In dichloromethane; at 20℃;Inert atmosphere;	General procedure: To a solution of the 1-adamantane carbonyl chloride (0.50 mmol, 1.06 equiv) in DCM (5 mL) was added triethylamine (0.15 mL), followed by the corresponding amine (0.47 mmol, 1 equiv). The reaction mixture was stirred at ambient temperature under nitrogen overnight. PS-Trisamine (10-20 mg) was added. After stirring at ambient temperature for another 2 h, the mixture was filtered and evaporation of the solvent gave a residue that was purified by flash chromatography (ethyl acetate-DCM gradient elution) to give the desired carboxamide derivatives.

Reference： [1]Bioorganic and medicinal chemistry,2012,vol. 20,p. 6394 - 6402,9

50
[ 156-81-0 ]
[ 2094-72-6 ]
[ 1403388-89-5 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 9609 - 9619

51
[ 2094-72-6 ]
[ 42105-26-0 ]
C₁₅H₂₁NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In acetonitrile; at 20℃; for 0.5h;	General procedure: To a solution of tetrahydro-2H-pyran-4-carbonyl chloride (100 mg, 0.7 mmol) in ACN (1.5 mL, 0.5 M) was added <strong>[42105-26-0]but-3-yn-2-amine hydrochloride</strong> (107 mg, 1.01 mmol) followed by triethylamine (142 muL, 1.01 mmol). The reaction mixture was stirred at room temperature for 30 min. AuCl3 (10 mg, 0.034 mmol) was added and the reaction mixture was stirred at 45 C for 2-3 h until complete conversion to the product which was detected by LCMS. After filtration and concentration, the crude oil was purified directly on SiO2 (12 g column eluted with 0-25% ethyl acetate-heptanes) to give a clear oil of 4,5-dimethyl-2-(tetrahydro-2H-pyran-4-yl)oxazole (83 mg, 68% yield).

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 259 - 261

52
[ 33893-89-9 ]
[ 2094-72-6 ]
[ 828-51-3 ]
[ 1415251-74-9 ]

Yield	Reaction Conditions	Operation in experiment
50%	With pyridine;Inert atmosphere; Reflux;	The reaction was performed with 5-(2'-pyridyl)-1H-tetrazole (500 mg, 3.40 mmol) and 1-adamantanecarboxylic acid chloride (675 mg, 3.40 mmol, Acros) in pyridine (3.5 mL). The reaction mixture was extracted with ether/H2O. The organic layer was washed with water (to remove pyridine) and evaporated. Purification by column chromatography was performed on silica (10 g). Elution with CH2Cl2 removed the impurities. Elution with 0.5% of CH3OH in CH2Cl2 recovered the product. It was re-dissolved in ether, and hexane (20 mL) was added. The ether was rotor-evaporated to leave a suspension of the product in hexane. The suspension was cooled to -15 C overnight and filtered. The product was washed with cold hexane. The product purified in this way contained 10% of 1-adamantanecarboxylic acid (detected by 1H and 13C NMR). To remove the acid, the product was sonicated in saturated aqueous solution of Na2CO3 for 10 min and extracted with ether. The organic layer was washed with saturated aqueous solution of Na2CO3 and water. It was evaporated, and the extraction with Na2CO3 (aq. sat.) and ether was repeated one more time. White solid: 477 mg (1.70 mmol, 50%). Anal. Calc. for C17H19N3O (MW 281.35): C, 72.57; H, 6.81; N, 14.94. Found: C, 72.54; H, 6.87; N, 14.74%. 1H NMR (400 MHz, [D6]dmso): delta = 8.79-8.74 (m, 1H), 8.19-8.13 (m, 1H), 8.03 (td, J = 8.0, 1.6 Hz, 1H), 7.62 (ddd, J = 7.6, 4.8, 1.2 Hz, 1H), 2.10-2.04 (m, br, 9H), 1.77 (br, 6H) ppm. 13C NMR (100 MHz, CD2Cl2): delta = 173.68, 163.90, 150.34, 144.25, 137.28, 125.72, 123.00, 40.12, 36.44, 34.71, 28.13 ppm. GC-EI+ MS: m/z 281 (M+, 100%).

Reference： [1]Inorganica Chimica Acta,2013,vol. 394,p. 295 - 299

53
[ 1914-02-9 ]
[ 2094-72-6 ]
[ 1422444-08-3 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 4h;	General procedure: A mixture of 24.5 mg (0.18 mmol) 1,2,3,4-tetrahydroquinoline, 37.3 mg (0.188 mmol) 1-adamatanecarbonyl chloride and 44.4 mg (0.34 mmol) DIPEA in 1 mL DCM was shaken at room temperature for 4 h. The mixture was evaporated, dissolved in DMF and subjected to column chromatography on reversed phase eluting with a gradient formed from acetonitrile, water and formic acid to yield after evaporation of the product containing fractions 34.9 mg (64%) of the title compound as white solid.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1177 - 1181

54
[ 59529-21-4 ]
[ 2094-72-6 ]
[ 1345973-49-0 ]

Reference： [1]ACS Chemical Neuroscience,2013,vol. 4,p. 1081 - 1092

55
[ 4295-36-7 ]
[ 2094-72-6 ]
[ 883841-97-2 ]

Yield	Reaction Conditions	Operation in experiment
22%	With pyridine; In 1,4-dioxane; at 110℃; for 16h;	Example 3 l-(Adamantane-l-carbonyl)-2,3-dihydro-lH-quinolin-4-one A mixture of 25.2 mg (0.17 mmol) 2,3-dihydroquinolin-4(lH)-one and 52.9 mg (0.26 mmol) adamatanecarbonyl chloride in 0.9 mL dioxane and 0.041 mL pyridine was shaken at 110 C for 16 h. The mixture was evaporated, dissolved in DMF and subjected to column chromatography on reversed phase eluting with a gradient formed from acetonitrile, water and formic acid to yield after evaporation of the product containing fractions 11.5 mg (22 %) of the title compound as white solid. MS(m/e): 310.4 (MH+).
22%	With pyridine; In 1,4-dioxane; at 110℃; for 16h;	Example 3 1-(Adamantane-1-carbonyl)-<strong>[4295-36-7]2,3-dihydro-1H-quinolin-4-one</strong> A mixture of 25.2 mg (0.17 mmol) <strong>[4295-36-7]2,3-dihydroquinolin-4(1H)-one</strong> and 52.9 mg (0.26 mmol) adamatanecarbonyl chloride in 0.9 mL dioxane and 0.041 mL pyridine was shaken at 110 C. for 16 h. The mixture was evaporated, dissolved in DMF and subjected to column chromatography on reversed phase eluting with a gradient formed from acetonitrile, water and formic acid to yield after evaporation of the product containing fractions 11.5 mg (22%) of the title compound as white solid. MS(m/e): 310.4 (MH+).

Reference： [1]Patent: WO2014/5968,2014,A1 .Location in patent: Page/Page column 18-19
[2]Patent: US2015/111886,2015,A1 .Location in patent: Paragraph 0190

56
[ 42882-31-5 ]
[ 2094-72-6 ]
[ 1528744-78-6 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In cyclohexane; at 10℃; for 6h;	General procedure: The N-acylation of racemic 1, 2, and 3 was carried out with acyl chlorides as acylation reagents and triethylamine as the base in cyclohexane in the presence and absence of TIPS-beta-CD. After a mixture of racemic 1, 2, and 3 (6.0x10-4 mmol) and 6-O-silylated beta-CD was stirred for 1 h in cyclohexane (600 muL) to reach the complexation equilibrium between 1, 2, and 3 and 6-O-silylated beta-CD, triethylamine (6.0x10-4 mmol), the acyl chlorides 4a-j were added at 10 C. The mixture was then stirred at 10 C for 6 h. The resulting products were analyzed by HPLC using the chiral phase column Diacel Chiralcel OD-H (250mm x4.6mm i.d.) using hexane/2-propanol=80:20 or 95:5 as an eluent at a flow rate of 0.5 or 1.5 mL min-1 using UV detection (254 nm). The HPLC charts of the products obtained after N-acylation of 1, 2, and 3 (6.0x10-4 mmol) with acyl chlorides 4a-j (3.3x10-4 mmol) in cyclohexane (600 muL)including triethylamine (6.0x10-4 mmol) in the absence and presence of TIPS-beta-CD (3.0x10-3 mmol) are shown in Figs. S18-26,respectively

Reference： [1]Tetrahedron,2014,vol. 70,p. 197 - 203

57
[ 42882-31-5 ]
[ 2094-72-6 ]
[ 10420-89-0 ]
[ 3886-70-2 ]
[ 138590-24-6 ]
C₂₃H₂₇NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With heptakis (6-O-triisopropylsilyl)-beta-cyclodextrin; triethylamine; In cyclohexane; at 10℃; for 6h;Resolution of racemate;	General procedure: The N-acylation of racemic 1, 2, and 3 was carried out with acyl chlorides as acylation reagents and triethylamine as the base in cyclohexane in the presence and absence of TIPS-beta-CD. After a mixture of racemic 1, 2, and 3 (6.0x10-4 mmol) and 6-O-silylated beta-CD was stirred for 1 h in cyclohexane (600 muL) to reach the complexation equilibrium between 1, 2, and 3 and 6-O-silylated beta-CD, triethylamine (6.0x10-4 mmol), the acyl chlorides 4a-j were added at 10 C. The mixture was then stirred at 10 C for 6 h. The resulting products were analyzed by HPLC using the chiral phase column Diacel Chiralcel OD-H (250mm x4.6mm i.d.) using hexane/2-propanol=80:20 or 95:5 as an eluent at a flow rate of 0.5 or 1.5 mL min-1 using UV detection (254 nm). The HPLC charts of the products obtained after N-acylation of 1, 2, and 3 (6.0x10-4 mmol) with acyl chlorides 4a-j (3.3x10-4 mmol) in cyclohexane (600 muL)including triethylamine (6.0x10-4 mmol) in the absence and presence of TIPS-beta-CD (3.0x10-3 mmol) are shown in Figs. S18-26,respectively

Reference： [1]Tetrahedron,2014,vol. 70,p. 197 - 203

58
[ 2094-72-6 ]
[ 361442-00-4 ]

Reference： [1]Letters in Organic Chemistry,2014,vol. 11,p. 627 - 631

59
[ 2744-08-3 ]
[ 2094-72-6 ]
(1-decahydroisoquinolinyl)(tricyclo[3.3.1.1^3,7]dec-1-yl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 4h;	DIPEA (1 .93ml, 1 1 .1 mmol) was added to a solution of Tricyclo[3.3.1.13,7]decane-1 - carbonyl chloride (1 ) (2g, 10.1 mmol) and <strong>[2744-08-3]decahydroisoquinoline</strong> (3) (1.59ml, 1 1 .1 mmol) in DCM (20ml) and the solution stirred at room temperature for 4 hours. At this time, TLC [15:85 EA:hexane, 20muIota_ aliquot into MTBE:1 N HCI (400muIota_:400muIota_)] showed the formation of a single product. The solution was washed with 0.1 N HCI (30ml), saturated NaHC03 (30ml), dried (Na2S04), filtered and the solvents removed to give crude product which was further purified by FC on silica gel using 15:85 EA:hexane to give the desired product as a white solid.
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 4h;	DIPEA (1 .93ml, 1 1 .1 mmol) was added to a solution of Tricyclo[3.3.1.13,7]decane-1 - carbonyl chloride (1 ) (2g, 10.1 mmol) and <strong>[2744-08-3]decahydroisoquinoline</strong> (3) (1.59ml, 1 1 .1 mmol) in DCM (20ml) and the solution stirred at room temperature for 4 hours. At this time, TLC [15:85 EA:hexane, 20muIota_ aliquot into MTBE:1 N HCI (400muIota_:400muIota_)] showed the formation of a single product. The solution was washed with 0.1 N HCI (30ml), saturated NaHC03 (30ml), dried (Na2S04), filtered and the solvents removed to give crude product which was further purified by FC on silica gel using 15:85 EA:hexane to give the desired product as a white solid.
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 4h;	DIPEA (1.93 ml, 11.1 mmol) was added to a solution of Tricyclo[3.3.1.13,7]decane-1-carbonyl chloride (1) (2 g, 10.1 mmol) and <strong>[2744-08-3]decahydroisoquinoline</strong> (3) (1.59 ml, 11.1 mmol) in DCM (20 ml) and the solution stirred at room temperature for 4 hours. At this time, TLC [15:85 EA:hexane, 20 muL aliquot into MTBE:1 N HCl (400 muL:400 muL)] showed the formation of a single product. The solution was washed with 0.1 N HCl (30 ml), saturated NaHCO3 (30 ml), dried (Na2SO4), filtered and the solvents removed to give crude product which was further purified by FC on silica gel using 15:85 EA:hexane to give the desired product as a white solid.

Reference： [1]Patent: WO2014/139965,2014,A1 .Location in patent: Page/Page column 23
[2]Patent: WO2014/139952,2014,A2 .Location in patent: Page/Page column 21; 22
[3]Patent: US2016/8249,2016,A1 .Location in patent: Paragraph 0114-0115

60
[ 2094-72-6 ]
[ 38646-68-3 ]
[ 82679-32-1 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 4h;	DIPEA (1 .93ml, 1 1 .1 mmol) was added to a solution of Tricyclo[3.3.1.13,7]decane-1 - carbonyl chloride (1 ) (1 g, 5.5mmol) and <strong>[38646-68-3]4,4-dimethylpiperidine hydrochloride</strong> (4) (828mg, 5.5mmol) in DCM (10ml) and the solution stirred at room temperature for 4 hours. At this time, TLC [15:85 EA:hexane, 20muIota_ aliquot into MTBE:1 N HCI (400muIota_:400muIota_)] showed the formation of a single chemical. The solution was washed with 0.1 N HCI (30ml), saturated NaHC03 (30ml), dried (Na2S04), filtered and the solvents removed to give crude product which was further purified by FC on silica gel using 15:85 EA:hexane to give the desired product as a crystalline white solid.
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 4h;	DIPEA (1 .93ml, 1 1 .1 mmol) was added to a solution of Tricyclo[3.3.1.13,7]decane-1 - carbonyl chloride (1 ) (1 g, 5.5mmol) and <strong>[38646-68-3]4,4-dimethylpiperidine hydrochloride</strong> (4) (828mg, 5.5mmol) in DCM (10ml) and the solution stirred at room temperature for 4 hours. At this time, TLC [15:85 EA:hexane, 20muIota_ aliquot into MTBE:1 N HCI (400muIota_:400muIota_)] showed the formation of a single chemical. The solution was washed with 0.1 N HCI (30ml), saturated NaHC03 (30ml), dried (Na2S04), filtered and the solvents removed to give crude product which was further purified by FC on silica gel using 15:85 EA:hexane to give the desired product as a crystalline white solid.
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 4h;	DIPEA (1.93 ml, 11.1 mmol) was added to a solution of Tricyclo[3.3.1.13,7]decane-1-carbonyl chloride (1) (1 g, 5.5 mmol) and <strong>[38646-68-3]4,4-dimethylpiperidine hydrochloride</strong> (4) (828 mg, 5.5 mmol) in DCM (10 ml) and the solution stirred at room temperature for 4 hours. At this time, TLC [15:85 EA:hexane, 20 muL aliquot into MTBE:1 N HCl (400 muL:400 muL)] showed the formation of a single chemical. The solution was washed with 0.1 N HCl (30 ml), saturated NaHCO3 (30 ml), dried (Na2SO4), filtered and the solvents removed to give crude product which was further purified by FC on silica gel using 15:85 EA:hexane to give the desired product as a crystalline white solid.

Reference： [1]Patent: WO2014/139965,2014,A1 .Location in patent: Page/Page column 24
[2]Patent: WO2014/139952,2014,A2 .Location in patent: Page/Page column 22
[3]Patent: US2016/8249,2016,A1 .Location in patent: Paragraph 0116-0117

61
[ 88675-24-5 ]
[ 2094-72-6 ]
((3-aminotetrahydrofuranyl)tricyclo[3.3.1.1^3,7]dec-1-yl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 4h;	DIPEA (1 .93ml, 1 1 .1 mmol) was added to a solution of Tricyclo[3.3.1.13,7]decane-1 - carbonyl chloride (1 ) (2g, 10.1 mmol) and <strong>[88675-24-5]3-aminotetrahydrofuran</strong>; (29)(1 .0ml, 1 1 mmol) in DCM (20ml) and the solution stirred at room temperature for 4 hours. The solution was washed with 0.1 N HCI (30ml), saturated NaHC03 (30ml), dried (Na2S04), filtered and the solvents removed to give crude product which was further purified via crystallization from 15percent EA in hexanes to give as a white solid
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 4h;	DIPEA (1 .93ml, 1 1 .1 mmol) was added to a solution of Tricyclo[3.3.1.13,7]decane-1 - carbonyl chloride (1 ) (2g, 10.1 mmol) and <strong>[88675-24-5]3-aminotetrahydrofuran</strong>; (29)(1 .0ml, 1 1 mmol) in DCM (20ml) and the solution stirred at room temperature for 4 hours. The solution was washed with 0.1 N HCI (30ml), saturated NaHC03 (30ml), dried (Na2S04), filtered and the solvents removed to give crude product which was further purified via crystallization from 15percent EA in hexanes to give as a white solid
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 4h;	DIPEA (1.93 ml, 11.1 mmol) was added to a solution of Tricyclo[3.3.1.13,7]decane-1-carbonyl chloride (1) (2 g, 10.1 mmol) and <strong>[88675-24-5]3-aminotetrahydrofuran</strong>; (29)(1.0 ml, 11 mmol) in DCM (20 ml) and the solution stirred at room temperature for 4 hours. The solution was washed with 0.1N HCl (30 ml), saturated NaHCO3 (30 ml), dried (Na2SO4), filtered and the solvents removed to give crude product which was further purified via crystallization from 15percent EA in hexanes to give as a white solid.

Reference： [1]Patent: WO2014/139965,2014,A1 .Location in patent: Page/Page column 36
[2]Patent: WO2014/139952,2014,A2 .Location in patent: Page/Page column 34
[3]Patent: US2016/8249,2016,A1 .Location in patent: Paragraph 0162-0163

62
[ 2094-72-6 ]
[ 52568-28-2 ]
(3r,5r,7r)-N-(2-(pyridin-2-yl)propan-2-yl)adamantane-1-carboxamide [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 1200 - 1203

63
[ 954255-04-0 ]
[ 2094-72-6 ]
[ 1533408-44-4 ]

Yield	Reaction Conditions	Operation in experiment
		Example 39 Adamantan-1-yl-(5,6-difluoro-2,3-dihydro-indol-1-yl)-methanone In analogy to the procedure described for the synthesis of adamantan-1-yl-(3,4-dihydro-1H-isoquinolin-2-yl)-methanone (example 1) the title compound was prepared from <strong>[954255-04-0]5,6-difluoroindoline</strong> and adamatanecarbonyl chloride as light brown solid. MS(m/e): 318.3 (MH+).

Reference： [1]Patent: US2015/111886,2015,A1 .Location in patent: Paragraph 0227

64
[ 17920-35-3 ]
[ 2094-72-6 ]
adamantan-1-yl(6-methoxy-3-methyl-2-phenyl-1H-pyrrolo[2,3-b]pyridin-1-yl)methanone [ No CAS ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 11202 - 11205

65
[ 17920-35-3 ]
[ 2094-72-6 ]
C₁₇H₂₂N₂O₂ [ No CAS ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 11202 - 11205

66
[ 27425-92-9 ]
[ 2094-72-6 ]
C₃₂H₅₈O₁₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃;Inert atmosphere;	1g of PEG monomethyl ester (PEG5000: 0.2mmol; PEG500: 2.1mmol) was dissolved in anhydrous DCM (PEG5000: 25ml; PEG500: 150ml) and cooled to 0C. Adamantane carbonyl chloride (5eq), DIPEA (10eq) and DMAP (1% cat.) were added and the mixture warmed to room temperature and stirred overnight under nitrogen. The mixture was transferred to a separating funnel and washed with 5% citric acid (50ml), saturated NaHCO3 (50ml), and brine (50ml). The organic layer was dried over MgSO4, filtered and concentrated in vacuo. Ad-PEG500 was purified by column chromatography over silica gel (DCM/MeOH: 9/1) to yield the product E as a yellow oil (1.1g, 83%). Ad-PEG5000 was dissolved in a minimum amount of DCM and precipitated from diethyl ether to yield the product F as a white solid (805mg, 78%).

Reference： [1]International Journal of Pharmaceutics,2016,vol. 499,p. 131 - 145

67
[ 40283-41-8 ]
[ 2094-72-6 ]
C₁₅H₁₈N₂O₃S [ No CAS ]

Reference： [1]PLoS ONE,2016,vol. 11

68
[ 770-71-8 ]
[ 2094-72-6 ]
C₂₃H₃₄O₂ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 10145 - 10149
Angew. Chem.,2016,vol. 128,p. 10300 - 10304,5

69
[ 2094-72-6 ]
[ 446065-11-8 ]
[ 77817-08-4 ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 1856 - 1863

70
[ 40359-32-8 ]
[ 2094-72-6 ]
4-haloaniline [ No CAS ]
N-(4-((3-(allyloxy)phenyl)(hydroxy)methyl)phenyl)adamantane-1-carboxamide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 4583 - 4587
Angew. Chem.,2017,vol. 129,p. 4654 - 4658,5

71
[ 611-05-2 ]
[ 2094-72-6 ]
adamantan-1-carboxylic acid-(3-methyl-4-nitrophenyl)amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With pyridine; at 0 - 20℃; for 3h;	[Example 1] Preparation of Adamantan-1-carboxylic acid-(3-methyl-4-nitrophenyl)-amide First, 3-methyl-4-nitroaniline (100 mg, 0.65 mmol, 1.1 eq) is dissolved into pyridine (1 ml). Next, adamantane carboxyl chloride (118 mg, 0.59 mmol, 1.0 eq) is added gradually dropwise thereto at 0C. The reaction mixture is agitated at room temperature for 3 hours. The reaction mixture is introduced to and diluted with ethyl acetate. Then, the reaction mixture is washed with 1N aqueous hydrochloric acid twice. After that, the reaction mixture is washed with saline, dried over dry manganese (100 mg), filtered, concentrated and separated by column chromatography to obtain 164 mg of the target product (yield 84%). The NMR results of the product are shown below. It can be seen from the NMR results that the product is adamantan-1-carboxylic acid-(3-methyl-4-nitrophenyl)-amide. 1H NMR (300MHz, CDCl3, delta): 8.03(d, 1 H, J = 9.0 Hz), 7.62(s, 1 H), 7.51-7.48(m, 2H), 2.62(s, 3H), 2.11 (s, 3H), 1.96-1.81(m, 6H), 1.81-1.71(m, 6H).

Reference： [1]Patent: EP3187486,2017,A1 .Location in patent: Paragraph 0084; 0085

72
[ 2094-72-6 ]
[ 454-67-1 ]
N-[3-fluoro-5-(trifluoromethyl)phenyl]adamantane-1-carboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 98 - 118

73
[ 2094-72-6 ]
[ 454-67-1 ]
N-[3-chloro-5-(trifluoromethyl)phenyl]adamantane-1-carboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 98 - 118

74
[ 2094-72-6 ]
[ 121148-01-4 ]
N-Boc-(4S)-(1-adamantylamido)-L-proline methyl ester [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 1621 - 1625

75
[ 1131-61-9 ]
[ 2094-72-6 ]
[ 939-23-1 ]
2,6-diadamantyl-4-phenylpyridine [ No CAS ]
[ 105398-73-0 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 3487 - 3490

76
[ 20098-14-0 ]
[ 2094-72-6 ]
C₂₁H₂₈O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		15.0 parts of the compound represented by the formula (I-1-a)22.4 parts of N-methylpiperidine,2.2 parts of dimethylaminopyridine and 45 parts of tetrahydrofuran were charged,Followed by stirring at 23 C. for 30 minutes.21.5 parts of the compound represented by the formula (I-1-b) was charged in the obtained mixture,Followed by stirring at 23 C. for 15 hours.To the resulting mixture,200 parts of ethyl acetate and 100 parts of a saturated aqueous ammonium chloride solution were charged,The mixture was stirred at 23 C. for 30 minutes,The organic layer was recovered by standing and liquid separation.To the recovered organic layer,100 parts of ion-exchanged water was charged,The mixture was stirred at 23 C. for 30 minutes,The organic layer was recovered by standing and liquid separation.This washing operation was repeated three times.The collected organic layer was concentrated.By collecting the concentrated mass on a column (Kanto Chemical Co., Ltd. Silica gel 60N (spherical, neutral) 100-210 mum developing solvent: n-heptane / ethyl acetate = 1/1)21.2 parts of a compound represented by the formula (I-1-c) was obtained.

Reference： [1]Patent: JP2016/117711,2016,A .Location in patent: Paragraph 0234

77
[ 50397-74-5 ]
[ 2094-72-6 ]
C₁₈H₁₉BrN₂O [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 12131 - 12135
Angew. Chem.,2018,vol. 130,p. 12307 - 12311,5

78
[ 887267-47-2 ]
[ 2094-72-6 ]
C₁₈H₁₉BrF₃NO₂ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 12131 - 12135
Angew. Chem.,2018,vol. 130,p. 12307 - 12311,5

79
[ 2094-72-6 ]
[ 4651-93-8 ]
methyl 2-[((adamantan-1-yl)carbonyl)amino]-4,5-dimethylthiophene-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	In 1,4-dioxane;	General procedure: A solution of the appropriate acyl chloride (adamantane-2-carbonyl chloride or 4-substituted benzoyl chloride, 1.3mmol) in dry dioxane (3mL) was added dropwise to a solution of 7a-m, 15, 16, 17 (1.0mmol) in 10mL of the same solvent, maintained at 70C. After the addition was complete, the mixture was refluxed until the formation of hydrogen chloride stopped (1-18h). The solution was concentrated in vacuo and the residue was dissolved in DCM (30mL), washed with NaHCO3 solution (10mL), dried over anhydrous Na2SO4, and evaporated to dryness. The crude product was purified by recrystallization from MeOH or flash column chromatography on silica gel using the reported eluent system.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 161,p. 239 - 251

80
[ 2094-72-6 ]
[ 108354-78-5 ]
methyl 2-[((adamantan-1-yl)carbonyl)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	In 1,4-dioxane;	General procedure: A solution of the appropriate acyl chloride (adamantane-2-carbonyl chloride or 4-substituted benzoyl chloride, 1.3mmol) in dry dioxane (3mL) was added dropwise to a solution of 7a-m, 15, 16, 17 (1.0mmol) in 10mL of the same solvent, maintained at 70C. After the addition was complete, the mixture was refluxed until the formation of hydrogen chloride stopped (1-18h). The solution was concentrated in vacuo and the residue was dissolved in DCM (30mL), washed with NaHCO3 solution (10mL), dried over anhydrous Na2SO4, and evaporated to dryness. The crude product was purified by recrystallization from MeOH or flash column chromatography on silica gel using the reported eluent system.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 161,p. 239 - 251

81
[ 637336-53-9 ]
[ 2094-72-6 ]
methyl 4-[((adamantan-1-yl)carbonyl)amino]-1-methyl-1H-pyrazole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane;	General procedure: A solution of the appropriate acyl chloride (adamantane-2-carbonyl chloride or 4-substituted benzoyl chloride, 1.3mmol) in dry dioxane (3mL) was added dropwise to a solution of 7a-m, 15, 16, 17 (1.0mmol) in 10mL of the same solvent, maintained at 70C. After the addition was complete, the mixture was refluxed until the formation of hydrogen chloride stopped (1-18h). The solution was concentrated in vacuo and the residue was dissolved in DCM (30mL), washed with NaHCO3 solution (10mL), dried over anhydrous Na2SO4, and evaporated to dryness. The crude product was purified by recrystallization from MeOH or flash column chromatography on silica gel using the reported eluent system.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 161,p. 239 - 251

82
[ 14667-47-1 ]
[ 2094-72-6 ]
methyl 2-[((adamantan-1-yl)carbonyl)amino]pyridine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With triethylamine; In dichloromethane; for 18h;	A solution of 1-adamantanecarbonyl chloride (198mg, 1mmol) in dry DCM (1mL) was slowly added to a cooled (0-5C) solution of <strong>[14667-47-1]methyl 2-aminopyridine-3-carboxylate</strong> (14) (152mg, 1mmol) and TEA (210muL, 1.5mmol) in dry DCM (3mL). After stirrring for 18h, the solution was diluted with DCM (5mL), washed with saturated solution of NaHCO3 (5mL) and brine (5mL), then dried over anhydrous sodium sulfate, and evaporated to dryness. The crude residue was purified by recrystallization from MeOH to afford the title compound in 40% yield. Mp 183-184C. 1H NMR (200MHz, CDCl3): delta 10.88 (s, 1H), 8.64 (m, 1H), 8.30-8.27 (m, 1H), 7.04-7.01 (m, 1H), 3.94 (s, 3H), 2.10-2.02 (m, 9H), 1.76-1.74 (m, 6H). MS (ESI): m/z 337 [M+Na]+

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 161,p. 239 - 251

83
[ 2094-72-6 ]
[ 2133-40-6 ]
methyl ((3r,5r,7r)-adamantane-1-carbonyl)prolinate [ No CAS ]

Reference： [1]Chemistry - A European Journal,2019,vol. 25,p. 3119 - 3124

84
[ 2094-72-6 ]
[ 1501-84-4 ]

Reference： [1]Patent: CN109232270,2019,A
[2]Patent: CN109320425,2019,A
[3]Patent: CN109384679,2019,A

85
[ 1205-39-6 ]
[ 2094-72-6 ]
N-phenyl-N-o-tolyladamantane-1-carboxamide [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2019,vol. 2019,p. 4844 - 4854

86
[ 56613-81-1 ]
[ 2094-72-6 ]
N-((S)-2-hydroxy-2-phenylethyl)adamantane-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0℃; for 3.2h;Inert atmosphere;	A 25 mL round bottom flask equipped with a magnetic stir bar, was charged with (S)-(+)-2-amino-1-phenylethanol (0.485 grams, 3.53 mmol), N,N-diisopropylethyl amine (0.714 grams, 5.52 mmol), and CH2Cl2 (5 mL). The reaction flask containing the mixture was placed in an ice bath and allowed to equilibrate for 10 minutes while mixing at 300 r.p.m under nitrogen atmosphere. A separate flask was charged with of 1-adamantanecarbonyl chloride (0.756 grams, 3.81 mmol) and CH2Cl2 (5 mL). The 1-adamantanecarbonyl chloride solution was transferred to a 10 mL, pressure equalizing addition funnel which was connected to the 25 mL reaction flask and this solution was added to the reaction flask over 12 minutes. The reaction was mixed at 300 r.p.m. in the melting ice bath and under nitrogen atmosphere for 3 hr. The reaction mixture was added to a 125 mL separatory funnel following the reaction time period. The reaction mixture was extracted with 320 mL aliquots of 1N HCl solution and 125 mL aliquot of saturated NaCl solution. The organic phase was recovered and dried over anhydrous Na2SO4, filtered, and concentrated under vacuum at 35-40 C. to give 0.941 grams of the intermediate (3S,5S,7S)-N-((S)-2-hydroxy-2-phenylethyl) adamantane-1-carboxamide which was used in the next synthetic step without further purification. LC/MS (ESI) m/z=300 (MH+). 1H NMR (300 MHz, CD3OD): delta 1.65-2.10 (m, 16H), 3.28-3.51 (m, 2H), 4.76 (dd, 1H), 7.20-7.42 (m, 5H). 13C NMR (75 MHz, CD3OD): delta 28.22, 36.19, 38.71, 40.40, 46.58, 72.19, 125.86, 127.21, 127.88, 142.51, 179.70

Reference： [1]Patent: US2019/330141,2019,A1 .Location in patent: Paragraph 0180-0182; 0179

87
[ 3964-52-1 ]
[ 2094-72-6 ]
C₁₇H₂₀ClNO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: The appropriate aminophenol derivative (1.5 mmol) was dissolvedin acetone (1.5 mL) under N2 (g), cooled to 0 C, charged with K2CO3(622 mg, 4.5 mmol), and stirred for 15 min. After that, the appropriateacyl chloride (1.55 mmol) dissolved in acetone (1 mL) was addeddropwise to the reaction mixture at 0 C. The reaction was monitored byTLC and LC-MS spectrometry. Once reaction completion was confirmed,the mixture was filtered, and the filtrate was concentrated invacuo. The solid was extracted using ethyl acetate (10 mL) and brine(10 mL). The organic layer was collected and dried over anhydrousNa2SO4 and concentrated in vacuo. The product was sulfamoylatedwithout further purification

Reference： [1]Bioorganic and medicinal chemistry,2020

88
[ 2835-99-6 ]
[ 2094-72-6 ]
C₁₈H₂₃NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: The appropriate aminophenol derivative (1.5 mmol) was dissolvedin acetone (1.5 mL) under N2 (g), cooled to 0 C, charged with K2CO3(622 mg, 4.5 mmol), and stirred for 15 min. After that, the appropriateacyl chloride (1.55 mmol) dissolved in acetone (1 mL) was addeddropwise to the reaction mixture at 0 C. The reaction was monitored byTLC and LC-MS spectrometry. Once reaction completion was confirmed,the mixture was filtered, and the filtrate was concentrated invacuo. The solid was extracted using ethyl acetate (10 mL) and brine(10 mL). The organic layer was collected and dried over anhydrousNa2SO4 and concentrated in vacuo. The product was sulfamoylatedwithout further purification

Reference： [1]Bioorganic and medicinal chemistry,2020

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 2094-72-6 ] {[proInfo.proName]}

Quality Control of [ 2094-72-6 ]

Related Doc. of [ 2094-72-6 ]

Product Details of [ 2094-72-6 ]

Safety of [ 2094-72-6 ]

Application In Synthesis of [ 2094-72-6 ]

[ 2094-72-6 ] Synthesis Path-Upstream 1~5

[ 2094-72-6 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 2094-72-6 ]

Aliphatic Cyclic Hydrocarbons

Chlorides

Acyl Chlorides

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 2094-72-6 ]